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Cheap flights from Chicago Midway Airport to San José from $143

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 12/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:30 am - 3:30 pmMDW-SJO
9h 00m1 stop
Multiple Airlines Logo
3:05 pm - 2:05 pmSJO-MDW
23h 00m2 stops
$305Multiple Airlines
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Thu, Feb 19 - Wed, Feb 25
Multiple Airlines Logo
6:30 am - 3:30 pmMDW-SJO
9h 00m1 stop
Multiple Airlines Logo
8:05 pm - 2:05 pmSJO-MDW
42h 00m2 stops
$318Multiple Airlines
Find Deal
Thu, Feb 19 - Tue, Feb 24
Multiple Airlines Logo
6:30 am - 6:55 pmMDW-SJO
12h 25m2 stops
Multiple Airlines Logo
2:58 pm - 11:25 pmSJO-MDW
8h 27m1 stop
$324Multiple Airlines
Find Deal
Thu, Feb 19 - Sat, Feb 28
Multiple Airlines Logo
3:02 pm - 11:40 amMDW-SJO
20h 38m2 stops
Multiple Airlines Logo
11:35 am - 9:58 pmSJO-MDW
9h 23m1 stop
$326Multiple Airlines
Find Deal
Sun, Mar 1 - Wed, Mar 11
Multiple Airlines Logo
6:30 am - 3:30 pmMDW-SJO
9h 00m1 stop
Multiple Airlines Logo
2:58 pm - 11:25 pmSJO-MDW
8h 27m1 stop
$328Multiple Airlines
Find Deal
Thu, Feb 19 - Sat, Feb 28
Multiple Airlines Logo
8:56 pm - 11:40 amMDW-SJO
14h 44m1 stop
Multiple Airlines Logo
2:58 pm - 11:25 pmSJO-MDW
8h 27m1 stop
$336Multiple Airlines
Find Deal
Fri, Feb 20 - Sat, Feb 28
Frontier Logo
6:12 am - 1:42 pmMDW-SJO
7h 30m1 stop
Frontier Logo
1:35 pm - 10:27 pmSJO-MDW
8h 52m1 stop
$342Frontier
Find Deal
Wed, Dec 31 - Sat, Jan 10
Multiple Airlines Logo
8:56 pm - 11:40 amMDW-SJO
14h 44m1 stop
Multiple Airlines Logo
11:35 am - 9:58 pmSJO-MDW
9h 23m1 stop
$345Multiple Airlines
Find Deal
Sun, Mar 1 - Wed, Mar 11
Frontier Logo
6:00 am - 1:52 pmMDW-SJO
7h 52m1 stop
Frontier Logo
10:36 am - 9:04 pmSJO-MDW
10h 28m1 stop
$348Frontier
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Sat, Dec 13 - Sat, Dec 20
Frontier Logo
12:41 pm - 1:36 pmMDW-SJO
24h 55m1 stop
Frontier Logo
3:12 pm - 8:03 amSJO-MDW
16h 51m1 stop
$352Frontier
Find Deal
Sun, Jan 11 - Sat, Jan 17

Frontier flights from Chicago Midway Airport to San José

Our best Frontier deals on Chicago Midway Airport to San José flight tickets
Frontier
Dec 31
MDW6:12 amChicago Midway
7h 30m
1 stop
SJO1:42 pmSan José Juan Santamaria Intl
Jan 10
SJO1:35 pmSan José Juan Santamaria Intl
8h 52m
1 stop
MDW10:27 pmChicago Midway
$342
Find similar
Frontier
Dec 13
MDW6:00 amChicago Midway
7h 52m
1 stop
SJO1:52 pmSan José Juan Santamaria Intl
Dec 20
SJO10:36 amSan José Juan Santamaria Intl
10h 28m
1 stop
MDW9:04 pmChicago Midway
$348
Find similar
Frontier
Jan 11
MDW12:41 pmChicago Midway
24h 55m
1 stop
SJO1:36 pmSan José Juan Santamaria Intl
Jan 17
SJO3:12 pmSan José Juan Santamaria Intl
16h 51m
1 stop
MDW8:03 amChicago Midway
$352
Find similar

Delta flights from Chicago Midway Airport to San José

Our best Delta deals on Chicago Midway Airport to San José flight tickets
Delta
Jan 20
MDW6:00 amChicago Midway
16h 15m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
Feb 4
SJO2:31 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:22 pmChicago Midway
$357
Find similar
Delta
Jan 20
MDW1:31 pmChicago Midway
8h 44m
2 stops
SJO10:15 pmSan José Juan Santamaria Intl
Jan 22
SJO7:00 amSan José Juan Santamaria Intl
10h 29m
1 stop
MDW5:29 pmChicago Midway
$361
Find similar
Delta
Feb 9
MDW10:46 amChicago Midway
11h 29m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
Feb 23
SJO7:00 amSan José Juan Santamaria Intl
15h 42m
1 stop
MDW10:42 pmChicago Midway
$384
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 1, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 2/19

6:30 am-3:30 pm

1 stop9h 00m

San José Juan Santamaria Intl

Wed 2/25

3:05 pm-2:05 pm

2 stops23h 00m

$305

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 2/19

6:30 am-3:30 pm

1 stop9h 00m

San José Juan Santamaria Intl

Tue 2/24

8:05 pm-2:05 pm

2 stops42h 00m

$318

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 2/19

6:30 am-6:55 pm

2 stops12h 25m

San José Juan Santamaria Intl

Sat 2/28

2:58 pm-11:25 pm

1 stop8h 27m

$324

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 3/1

3:02 pm-11:40 am

2 stops20h 38m

San José Juan Santamaria Intl

Wed 3/11

11:35 am-9:58 pm

1 stop9h 23m

$326

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 2/19

6:30 am-3:30 pm

1 stop9h 00m

San José Juan Santamaria Intl

Sat 2/28

2:58 pm-11:25 pm

1 stop8h 27m

$328

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 2/20

8:56 pm-11:40 am

1 stop14h 44m

San José Juan Santamaria Intl

Sat 2/28

2:58 pm-11:25 pm

1 stop8h 27m

$336

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 12/31

6:12 am-1:42 pm

1 stop7h 30m

San José Juan Santamaria Intl

Sat 1/10

1:35 pm-10:27 pm

1 stop8h 52m

$342

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 3/1

8:56 pm-11:40 am

1 stop14h 44m

San José Juan Santamaria Intl

Wed 3/11

11:35 am-9:58 pm

1 stop9h 23m

$345

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 12/13

6:00 am-1:52 pm

1 stop7h 52m

San José Juan Santamaria Intl

Sat 12/20

10:36 am-9:04 pm

1 stop10h 28m

$348

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 1/11

12:41 pm-1:36 pm

1 stop24h 55m

San José Juan Santamaria Intl

Sat 1/17

3:12 pm-8:03 am

1 stop16h 51m

$352

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to San José?

On average, the least expensive day to fly to San José from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $542. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to San José on a Saturday will generally be more expensive and average around $746. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José?

Our data shows that the cheapest Chicago Midway Airport to San José flights are usually those with departure times in the evening. Our users have found flights to San José in the evening for as low as $453. Flights in the morning are often more expensive with an average ticket price of $705.

When to book flights from Chicago Midway Airport to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José

Fastest flight time

6h 55m

Direct flights

None
The fastest flight from Chicago Midway Airport to San José takes 6h 55m
There are no direct flights from Chicago Midway Airport to San José. There are no popular flight routes from Chicago Midway Airport to San José.
Search flight deals

  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 7h 30m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José?

Best airlines flying from Chicago Midway Airport to San José

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $394Free CancellationRating
8.0
4,253 reviews
Search Southwest flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Alajuela
Monteverde
Heredia
Dominical
Santa Elena
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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